Tag: M.W=200-300

49764-63-8, Adding a certain compound to certain chemical reactions, such as: 49764-63-8, name is 4,5-Dibromobenzene-1,2-diamine, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 49764-63-8.

General procedure: Intermediate1 (3.17 g, 8.7 mmol) and 4,5-dibromobenzene-1,2-diamine (3.02 g, 11.35 mmol) were dissolved in 90 mL acetic acid,and then heated to reflux for 16 h. After cooling down, the resultingmixture was poured into water and neutralized by sodium hydroxide.The suspension was extracted with chloroform(50 mL 3), and the combined organic layer was washed withwater and dried over anhydrous sodium sulfate. After that, thesolvent was removed by vacuum distillation and the rest solid waspurified with a silica gel column. Using dichloromethane/methanol(v/v) 20:1 as eluent and gave the target compound as light yellowsolid (4.3 g, yield: 83%).

According to the analysis of related databases, 49764-63-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yin, Xiaojun; Sun, Hengda; Zeng, Weixuan; Xiang, Yepeng; Zhou, Tao; Ma, Dongge; Yang, Chuluo; Organic electronics; vol. 37; (2016); p. 439 – 447;,
Bromide – Wikipedia,
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627871-16-3, The chemical industry reduces the impact on the environment during synthesis 627871-16-3, name is 5-Bromo-4-fluoro-2-methylaniline, I believe this compound will play a more active role in future production and life.

To a suspension [OF 5-BROMO-4-FLUORO-2-METHYLANILINE (11.] 2 g, 54.9 mmol) in concentrated [HCL] (35 mL) was added dropwise a solution of sodium nitrite (4.17 g, 60.4 mmol) in water (20 mL) over 30 minutes at [0C.] To the mixture was added dropwise a solution [OF SNCI2*2H2O] (37.2 g, 165 mmol) in concentrated HCl (45 mL) over 1 hour. After stirring for 2 hours at 0 [C,] the reaction mixture was basified with 50% NaOH (50 mL). The mixture was further diluted with water (50 mL) and treated with another 50% NaOH (20 mL) and then crushed ice (200 g). The reaction mixture was extracted with ether (3 x 200 mL) and the combined organic phases were washed with brine, dried over [NA2SO4,] and filtered. The filtrate was acidified by adding an anhydrous solution of [HCL] in ether (2 N in ether, 42 mL, 82.5 mmol). The precipitate was collected and dried under reduced pressure to give 9.92 g [(71 %)] of title compound as a pale yellow [SOLID.’H] NMR (DMSO): 300 MHz [6] 10.18 (bs, 3H), 7.98 (bs, 1H), 7.21 (m, 2H), 2.16 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-4-fluoro-2-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; WYETH; VIROPHARMA INCORPORATED; WO2003/99824; (2003); A1;,
Bromide – Wikipedia,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 937046-98-5 as follows. 937046-98-5

To a suspension of the bromide 3 (prepared according to W02009/132135) (710 mg, 3.33 mmol) in dry THF (6.0 mE) was added 1,2-bis(chlorodimethylsilyl)ethane (717 mg, 3.33 mmol) in one portion at room temperature. Afier 1 h, the resulting slurry was cooled to -78 C. and n-l3uEi (7.5 mE of a 1.6M solution in hexanes, 12.0 mmol) was added dropwise over a 5 mm period. After stirring for 20 min at this temperature, a solution of 4 (1.0 g, 3.03 mmol) in dry THF (2.85 mE) was added dropwise over several minutes. The reaction was stirred at this temperature for 3 h and then allowed to warm to 0 C. Glacial HOAc (2.5 mE) was added and the reaction was warmed to room temperature. After vigorously stirring for 10 mm, the bulk of the solvents were removed under reduced pressure and the reaction mixture was partitioned between ethyl acetate and watet The layers were separated and the organic layer was washed with sat. NaHCO3, brine, dried over Na2504 and concentrated to provide a dark brown residue. Purification of the residue by flash column chromatography on silica gel using a gradient of 50% hexanes in ethyl acetate to 20% hexanes in ethyl acetate provided the desired product 5 (591 mg, 42%) as a pale yellow foam.

According to the analysis of related databases, 937046-98-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Sciences, Inc.; Clarke, Michael O’ Neil Hanrahan; Kim, Choung U.; Lew, Willard; (51 pag.)US2017/226140; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 937046-98-5, 937046-98-5

A mixture of 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (0.200 g, 0.939 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (0.279 g, 1.127 mmol), tripotassium phosphate (2 M in water) (1.408 mL, 2.82 mmol), and N,N- dimethylformamide (4.0 mL) was degassed with vacuum and nitrogen (3x).1,1′-Bis(di- tert-butylphosphino)ferrocene palladium dichloride (0.069 g, 0.094 mmol) was added, and the reaction mixture was degassed (2x). The reaction mixture was immediately immersed in an oil bath at 95 C and stirred overnight. The reaction mixture was cooled to rt and then diluted with water (2 mL) followed by 1N aqueous hydrochloric acid (2 mL), resulting in a precipitate. The solid was collected by vacuum filtration and dried under reduced pressure to give 3-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)benzoic acid (0.117 g, 0.460 mmol, 49.0 % yield) as a gray solid. (0980) MS ESI m/z 255.1 (M+H)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); A1;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 22385-77-9 name is 1-Bromo-3,5-di-tert-butylbenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 22385-77-9

A solution of 2,2,6,6-tetramethylpiperidine (2.0 mL, 12 mmol) in THF (12 mL) was treated with n-BuLi (7.5mL, 1.60 M in hexane, 12 mmol) at 0 ¡ãC. After stirring for 1 h at 0 ¡ãC the solution wasadded to a solution of bromoferrocene (1.32 g, 5.00 mmol) in THF (10 mL) at ?78 ¡ãC.After stirring for 30 min at ?78 ¡ãC and 3 h at ?30 ¡ãC the reaction mixture wastransferred to a suspension of ZnCl2 (1.36 g, 10.0 mmol) in THF (10 mL) at ?78 ¡ãC.Stirring was continued at ?78 ¡ãC for 30 min before the mixture was warmed to roomtemperature, where stirring was maintained for 30 min. To the resulting solution wasadded a solution of 1-bromo-3,5-di-t-butylbenzene (1.48 g, 5.50 mmol) and [Pd(PPh3)4](0.29 g, 0.25 mmol) in THF (10 mL). The reaction mixture was heated to 60 ¡ãC for 10hours, before the reaction was quenched with a saturated aqueous ammonium chloridesolution. The reaction mixture was extracted with hexane and the combined organicphases were washed with water and dried over MgSO4. After filtration, the filtrate wasevaporated to dryness under reduced pressure and the obtained residue was purified bycolumn chromatography on silica gel (hexane) to give compound 3 (2.01 g, 4.43 mmol,89percent). 3: orange solid; m.p. 87?89 ¡ãC; 1H NMR (300 MHz, CDCl3) delta 1.37 (s, 18H), 4.17(s, 5H), 4.22 (t, J = 2.6 Hz, 1H), 4.43 (dd, J = 2.6, 1.4 Hz), 4.54 (dd, J = 2.6, 1.4 Hz),7.33 (t, J = 1.8 Hz, 1H), 7.55 (d, J = 1.8 Hz, 2H); 13C NMR (75 MHz, CDCl3) delta 31.6 (q),34.8 (q), 66.3 (d), 67.5 (d), 71.0 (d), 72.0 (d), 78.3 (s), 87.7 (s), 120.8 (d), 123.9 (d),135.2 (s), 149.8 (s). Anal. Calcd for C24H29BrFe: C, 63.60; H, 6.45percent. Found: C, 63.84;H, 6.48percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 22385-77-9, and friends who are interested can also refer to it.

Reference:
Article; Sasamori, Takahiro; Suzuki, Yuko; Sakagami, Michiyasu; Miyake, Hideaki; Tokitoh, Norihiro; Chemistry Letters; vol. 43; 9; (2014); p. 1464 – 1466;,
Bromide – Wikipedia,
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51554-93-9, name is 1-Bromo-4-octylbenzene, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 51554-93-9

Pd(OAc)2 (0.232 mg, 1.032 mumol), and S-Phos (0.424 mg, 1.032 mumol) were added to a suspension of K2CO3 (35.7 mg, 0.258 mmol), 1-bromo-4-octylbenzene (0.012 ml, 0.052 mmol), 5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-[1,2′-bipyridin]-2-one (20 mg, 0.067 mmol) in acetonitrile/water (1.5:1). The suspension was degassed for 5 minutes and refluxed for 6 h. The reaction mixture was extracted with EtOAc, washed with brine, dried with MgSO4 and filtered. After evaporation of the organic solvent under reduced pressure, the resulting residue was purified by column chromatography over silica gel (100% hexanes to 40/60 hexanes/EtOAc) to provide the title compound as an off-white solid (81% yield). 1H NMR (400 MHz, CDCl3) delta 8.75 (t, J = 1.7 Hz, 1H), 8.00 (d, J = 1.6 Hz, 3H), 7.92 (dd, J = 2.1 Hz, 7.1 Hz, 1H), 7.52 (d, J = 8.3 Hz, 2H), 7.41 (m, 1H), 7.31 (d, J = 8.3 Hz, 2H), 6.71-6.63 (m, 1H), 6.36-6.27 (m, 1H), 2.66 (t, J = 7.8 Hz, 2H), 1.71-1.59 (m, 2H), 1.37-1.22 (m, 8H), 0.88 (t, J = 6.8 Hz, 3H); 13C NMR (101 MHz, CDCl3) delta 162.3, 150.5, 147.0, 143.5, 140.2, 136.3, 136.0, 135.9, 134.1, 129.3, 127.0, 122.1, 121.1, 106.3, 35.7, 31.9, 31.5, 29.5, 29.4, 29.3, 29.2, 22.7, 14.1; HRMS (ESI+) m/z calcd for C24H28N2O [M+Na]+ 383.2094, found 383.2113.

Statistics shows that 51554-93-9 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-4-octylbenzene.

Reference:
Article; Raje, Mithun R.; Knott, Kenneth; Kharel, Yugesh; Bissel, Philippe; Lynch, Kevin R.; Santos, Webster L.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 183 – 194;,
Bromide – Wikipedia,
bromide – Wiktionary

67567-26-4, name is 4-Bromo-2,6-difluoroaniline, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 67567-26-4

4-Bromo-2,6-difluoro-phenylamine (200 g, 0.961 mol) and N-isopropyl acetamide (107 g, 1.057 mol) in toluene (1000 mL) were stirring at 10-15 C. Phosphoryl chloride (177 g, 1.154 mol) and triethylamine (117 g, 1.156 moles) were slowly added. The reaction mixture was heated to reflux for 2-3 hours. The reaction mass was cooled to 10-15 C and water was slowly added into the reaction mixture which was stirred at 30-35 C for 15-20 minutes. The pH of the reaction mass was adjusted to 7.5-8.0 with a sodium hydroxide solution, stirred for 30 minutes at 30-35 C, and the layers were separated. The organic layer was washed with water and the layers were againseparated. Potassium hydroxide (161.5 g, 2.88 mol) and dimethylsulfoxide 400 mL at 30-35 Cwere charged to the organic layer. The reaction mixture was heated to reflux and water wasadded azeotropically for 2-4 hours at reflux temperature. The reaction mass was cooled to 25-30C and water was slowly added into the reaction mixture. The reaction mixture was stirred at 30-35 C for 15-20 minutes and the layers were separated. The organic layer was washed with anaqueous sodium chloride solution. The organic layer was concentrated under vacuum. Toluene (160 mL) and hexanes (1000 mL) were charged to the residue and the resulting mixture was stirred for 2-3 hours at room temperature. The mixture was filtered and the collected solid was washed with hexanes and dried at 50-55 C to yield 215 g (82.3%) of 6-bromo-4-fluoro-1- isopropyl-2-methyl-1H-benzoimidazole with a purity of 99.70%.

Statistics shows that 67567-26-4 is playing an increasingly important role. we look forward to future research findings about 4-Bromo-2,6-difluoroaniline.

Reference:
Patent; MYLAN LABORATORIES LIMITED; JETTI, Ramakoteswara Rao; INDUKURI, Anjaneyaraju; BOMMAREDDY, Aggi Ramireddy; SRINIVASARAO, Attanti Veera Venkata; JEBARAJ, Rathinapandian; CHANDUPATLA, Shivakumar; BATHARAJU, Ramesh; KUNAMNENI, Sunil; (74 pag.)WO2019/102492; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 68322-84-9

Example 43A 4-trans(2-bromo-4-trifluoromethyl-phenoxy)-cyclohexylamine To a stirred solution of trans-4-aminocyclohexanol (115 mg, 1 mmol) in DMF (3 mL) at 0 C. was added 60% NaH in mineral oil (120 mg, 3 mmol). The reaction mixture was stirred at 0 C. for 1/2 hour and then 3-bromo-4-fluoro-1-trifluoromethyl benzene (0.17 ml, 1.2 mmol) was added. It was heated to 60 C. for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) m/z 338 (M+H)+.

Statistics shows that 68322-84-9 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene.

Reference:
Patent; Madar, David J.; Djuric, Stevan W.; Michmerhuizen, Melissa J.; Kopecka, Hana A.; Li, Xiaofeng; Longenecker, Kenton L.; Pei, Zhonghua; Pireh, Daisy; Sham, Hing L.; Stewart, Kent D.; Szczepankiewicz, Bruce G.; Wiedeman, Paul E.; Yong, Hong; US2004/259843; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

58971-11-2, name is 3-Bromophenethylamine, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 58971-11-2

A mixture of 3-bromobenzeneethanamine (9.70 g, 48,5 mmole) and 2,6-lutidine (5.8 ml, 50.0 mmole) in dry CH2Cl2 (150 ml) was cooled to 0 0C. Trifluoroacetic anhydride (5.6 ml, 40 mmole) was added dropwise; the reaction was then warmed to room temperature and allowed to stir for 24 hours. Water (120 ml) was added to the reaction, the phases were separated, and the aqueous layer was extracted with CH2Cl2 (2 x 100 ml). The combined organic phases were washed successively with IN HCl (100 ml) and saturated NaHCO3 (100 ml), and then dried over Na2SO4, filtered, and concentrated in vacuo to provide the tile compound (12.3 g, 86%). The crude compound was used in subsequent steps. 1H NMR (400 MHz, CDCl3) delta 7.40 (d, J=8.0 Hz, IH), 7.36 (s, IH), 7.21 (t, J=7.6 Hz, IH), 7.12 (t, J=7.6 Hz, IH), 6.31 (br s, IH), 3.59 (q, J-6.8 Hz, 2H)5 2.87 (t, JK7.2 Hz, 2H).

Statistics shows that 58971-11-2 is playing an increasingly important role. we look forward to future research findings about 3-Bromophenethylamine.

Reference:
Patent; PREDIX PHARMACEUTICALS HOLDINGS, INC.; WO2007/61458; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

40161-54-4, A common compound: 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of l-bromo-2-fluoro-4-(trifluoromethyl)benzene (200 mg; 0.82 mmol)[CAS 40161-54-4] in tetrahydrofuran (15 mL) cooled to -70 C was added dropwise a solution of 1.6M n-butyllithium in n- hexane (0.7 mL; 1.1 mmol). After agitation at -70 C for 1 hour, the reaction mixture was treated dropwise with a solution of teri-butyl 4-[methoxy(methyl)carbamoyl]piperidine-l-carboxylate (247 mg; 0.91 mmol) [CAS 139290-70-3] in tetrahydrofuran (5 niL). The reaction mixture was stirred for 0.5 hours at -70 C and then for 2 hours at room temperature. The reaction mixture was deactivated with a saturated aqueous ammonium chloride solution (20 mL), then ethyl acetate (30 mL) was added. The organic layer was separated, dried over Na2S04, filtered and concentrated to dryness. The residue was purified by column chromatography (silica gel; petroleum ethenethyl acetate; 30:1 ; v/v) to afford teri-butyl 4-[2- fluoro-4-(trifluoromethyl)benzoyl]piperidine-l-carboxylate (180mg) as a white solid. MS m/z (+ESI): 320.1 [M-iBu+H]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASILEA PHARMACEUTICA INTERNATIONAL AG; LANE, Heidi; RICHALET, Florian; EL SHEMERLY, Mahmoud; (169 pag.)WO2018/2220; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary